Category: 114344-60-4

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 114344-60-4 as follows. Recommanded Product: 114344-60-4

A solution of 0.37g sodiumnitrite in 3ml of water is added at -5C to a solution of 1 g of 2-amino-3-bromo-benzonitrile (Synthetic Communications (1989), 19(13-14), 2255-63) in 8ml of concentrated hydrochloric acid. The mixture is stirred at -5C for 90min.In a separate flask a solution of 0.22 g of copper(ll) chloride dihydrate in 14 ml of glacial acetic acid is saturated with sulfur dioxide and then cooled to -8C. Then the mixture of with the diazonium salt is added dropwise at -8C to -3C and stirred for 2 hours.The reaction mixture is poured into ice cooled water. The aqueous layer is extracted three times with dichloromethane. The combined organic layers are dried over magnesium sulfate, filtered and concentrated in vacuo. The resulting residue is suspended in cyclohexane and filtered. The resulting residue is washed with cyclohexane and dried to afford 1.2 g of 2-bromo-6-cyano- benzenesulfonyl chloride.1H-NMR (CDCI3, 400 MHz): 8.15 (d, 1 H), 7.96 (d, 1 H), 7.67 (t, 1 H) ppm.

According to the analysis of related databases, 114344-60-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; WO2009/141305; (2009); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 114344-60-4, name is 2-Amino-3-bromobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of 2-Amino-3-bromobenzonitrile

General procedure: 9-Amino-4-X-5-bromo-2-(alkyl)-2,3-dihydropyrrolo[3,4-b]quinolin-1-one (X = H or F).A white slurry of 4-X-3-bromo-2-[1-(alkyl)-5-oxo-2,5-dihydro-1H-pyrrol-3-ylamino]-benzonitrile (1.0 equiv) in t-butanol (0.08-1.00 M) was warmed to 45 C and treated with sodium t-butoxide (1.2 equiv). The resulting green solution was heated at 45 C for 3 h. The reaction was cooled to room temperature, partitioned between methylene chloride and water and the organic layer was washed with saturated aqueous sodium bicarbonate and the combined aqueous layers were extracted with methylene chloride. The organic layers were washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure to give a light tan solid in greater than 80% yield, which was used without further purification.The intermediate compounds were prepared as follows:4-X-3-Bromo-2-[1-(alkyl)-5-oxo-2,5-dihydro-1H-pyrrol-3-ylamino]-benzonitrile (X = H or F).2-Amino-3-bromo-4-X-benzonitrile (1.0 equiv) and 1-(alkyl)-4-methoxy-1H-pyrrol-2(5H)-one (2.0 equiv) were combined in acetic acid (0.5-0.8 M benzonitrile in HOAc) and heated to 80 C. Methanesulfonic acid (2.5 equiv) was dissolved in acetic acid (10 M) and added dropwise via syringe over 15 min. The reaction was stirred for 1 h at 80 C and then cooled to rt and placed on a rotary evaporator under high vacuum for 15 min at 55 C to remove the acetic acid. The resulting oil was dissolved in methylene chloride and slowly added dropwise over 20 min to a solution of saturated aqueous sodium bicarbonate at 0-5 C, maintaining the pH value above 8. The resultant precipitate from the biphasic system was separated, washed with water twice and then with hexane once, and was dried at 50 C under high-vacuum to give a tan solid as the title compound in 70-85% yield, which was used without further purification (see Table 8).

The synthetic route of 114344-60-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Alhambra, Cristobal; Becker, Chris; Blake, Timothy; Chang, Amy; Damewood Jr., James R.; Daniels, Thalia; Dembofsky, Bruce T.; Gurley, David A.; Hall, James E.; Herzog, Keith J.; Horchler, Carey L.; Ohnmacht, Cyrus J.; Schmiesing, Richard Jon; Dudley, Adam; Ribadeneira, Maria D.; Knappenberger, Katherine S.; MacIag, Carla; Stein, Mark M.; Chopra, Maninder; Liu, Xiaodong F.; Christian, Edward P.; Arriza, Jeffrey L.; Chapdelaine, Marc J.; Bioorganic and Medicinal Chemistry; vol. 19; 9; (2011); p. 2927 – 2938;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Some common heterocyclic compound, 114344-60-4, name is 2-Amino-3-bromobenzonitrile, molecular formula is C7H5BrN2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. name: 2-Amino-3-bromobenzonitrile

3-Bromo-2-[1-(4-methoxybenzyl)-5-oxo-2,5-dihydro-1H-pyrrol-3-ylamino]-benzonitrileThe 4-methoxy-1-(4-methoxybenzyl)-1,5-dihydro-pyrrol-2-one (11.19 g, 48.0 mmol), 2-amino-3-bromobenzonitrile (11.83 g, 60.1 mmol), and p-toluene sulfonic acid (8.22 g, 43.2 mmol) were mixed together, ground to fine powder and transferred to a round-bottomed flask. The flask was placed in a preheated 130 C. oil bath and the reaction stirred for 40 minutes. The reaction mixture was removed from the bath, cooled, and dissolved in methylene chloride. The solution was washed with sodium bicarbonate (saturated aqueous solution) and the organic layer dried over sodium sulfate, filtered, and concentrated under reduced pressure to afford a brown solid (19.5 g). The crude material was purified by flash chromatography on silica gel eluting with a gradient of 20 to 40% ethyl acetate in methylene chloride to afford the desired compound (6.58 g, 34%). 1H NMR (300.132 MHz, DMSO) delta 9.10 (s, 1H), 8.07 (dd, J=8.1, 1.3 Hz, 1H), 7.92 (dd, J=7.7, 1.2 Hz, 1H), 7.40 (t, J=8.0 Hz, 1H), 7.15 (dt, J=8.6, 2.3 Hz, 2H), 6.91 (dt, J=8.9, 2.3 Hz, 2H), 4.44-4.37 (m, 3H), 3.88 (s, 2H), 3.74 (s, 3H). MS APCI, m/z=398/400 (M+H). HPLC 1.94 min.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 114344-60-4, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; US2008/318943; (2008); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 114344-60-4, name is 2-Amino-3-bromobenzonitrile, A new synthetic method of this compound is introduced below., Quality Control of 2-Amino-3-bromobenzonitrile

xample 11 – Synthesis of Compound 15; A solution of 1.39 g (7.04 mmol) 2-amino-3-bromo-benzonitrile (synthesis described in J. B. Campbell and T. W. Davenport, Syn. Commun. 19, 2255 [1989]) in 14 ml 1 – butanol was treated with 1.14 g (14.1 mmol) triazine and 1.2 ml acetic acid and heated to 110 C. The resulting solution was stirred for 4 days at this temperature. The reaction mixture was cooled to room temperature and evaporated. The residue was crystallized from tert.butyl-methyl-ether yielding 8-bromo-quinazolin-4-ylamine as brown solid; HPLC/MS: 1.00 min, [M+H] 224/226

The synthetic route of 114344-60-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK PATENT GMBH; DORSCH, Dieter; JONCZYK, Alfred; HOELZEMANN, Guenter; AMENDT, Christiane; ZENKE, Frank; WO2012/595; (2012); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route of 114344-60-4, A common heterocyclic compound, 114344-60-4, name is 2-Amino-3-bromobenzonitrile, molecular formula is C7H5BrN2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

General procedure: 9-Amino-4-X-5-bromo-2-(alkyl)-2,3-dihydropyrrolo[3,4-b]quinolin-1-one (X = H or F).A white slurry of 4-X-3-bromo-2-[1-(alkyl)-5-oxo-2,5-dihydro-1H-pyrrol-3-ylamino]-benzonitrile (1.0 equiv) in t-butanol (0.08-1.00 M) was warmed to 45 C and treated with sodium t-butoxide (1.2 equiv). The resulting green solution was heated at 45 C for 3 h. The reaction was cooled to room temperature, partitioned between methylene chloride and water and the organic layer was washed with saturated aqueous sodium bicarbonate and the combined aqueous layers were extracted with methylene chloride. The organic layers were washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure to give a light tan solid in greater than 80% yield, which was used without further purification.The intermediate compounds were prepared as follows:4-X-3-Bromo-2-[1-(alkyl)-5-oxo-2,5-dihydro-1H-pyrrol-3-ylamino]-benzonitrile (X = H or F).2-Amino-3-bromo-4-X-benzonitrile (1.0 equiv) and 1-(alkyl)-4-methoxy-1H-pyrrol-2(5H)-one (2.0 equiv) were combined in acetic acid (0.5-0.8 M benzonitrile in HOAc) and heated to 80 C. Methanesulfonic acid (2.5 equiv) was dissolved in acetic acid (10 M) and added dropwise via syringe over 15 min. The reaction was stirred for 1 h at 80 C and then cooled to rt and placed on a rotary evaporator under high vacuum for 15 min at 55 C to remove the acetic acid. The resulting oil was dissolved in methylene chloride and slowly added dropwise over 20 min to a solution of saturated aqueous sodium bicarbonate at 0-5 C, maintaining the pH value above 8. The resultant precipitate from the biphasic system was separated, washed with water twice and then with hexane once, and was dried at 50 C under high-vacuum to give a tan solid as the title compound in 70-85% yield, which was used without further purification (see Table 8).

The synthetic route of 114344-60-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Alhambra, Cristobal; Becker, Chris; Blake, Timothy; Chang, Amy; Damewood Jr., James R.; Daniels, Thalia; Dembofsky, Bruce T.; Gurley, David A.; Hall, James E.; Herzog, Keith J.; Horchler, Carey L.; Ohnmacht, Cyrus J.; Schmiesing, Richard Jon; Dudley, Adam; Ribadeneira, Maria D.; Knappenberger, Katherine S.; MacIag, Carla; Stein, Mark M.; Chopra, Maninder; Liu, Xiaodong F.; Christian, Edward P.; Arriza, Jeffrey L.; Chapdelaine, Marc J.; Bioorganic and Medicinal Chemistry; vol. 19; 9; (2011); p. 2927 – 2938;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 114344-60-4, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 114344-60-4 as follows.

3-Bromo-2-(1-((1s,3s)-3-methylcyclobutyl)-5-oxo-2,5-dihydro-1H-pyrrol-3-ylamino)benzonitrile4-Methoxy-1-((1s,3s)-3-methylcyclobutyl)-1H-pyrrol-2(5H)-one (4.20 g, 22.02 mmol) and 2-amino-3-bromobenzonitrile (5.94 g, 30.16 mmol) in acetic acid (15 mL) were warmed to 80 C. to give an amber solution. Methanesulfonic acid (3.57 mL, 55.04 mmol) in acetic acid (4 mL) was added drop wise into the reaction at 80 C. over one hour. After the addition, the reaction was stirred for another 30 minutes at 80 C. to complete. All of acetic acid was removed under high vacuum at 50 C. The residual was diluted in methylene chloride (150 mL) and then titrated into a half-saturated NaHCO3 aqueous solution at 0 C. slowly. The organic layer was dried through MgSO4, filtrated and evaporated to dry. The crude material was added to a silica gel column and was eluted with 0-10% methanol in methylene chloride to give an orange-yellow solid as the title compound (5.27 g, 68%) 1H NMR(300 MHz, CHLOROFORM-d) delta ppm 7.88 (dd, J=8.1, 1.4 Hz, 1 H) 7.67 (dd, J=7.7, 1.4 Hz, 1 H) 7.23 (t, J=8.01 Hz, 1 H) 6.02 (s, 1 H) 4.85 (s, 1 H) 4.39-4.63 (m, 1 H) 4.11 (s, 2 H) 2.29-2.50 (m, 2 H) 1.90-2.20 (m, 1 H) 1.59-1.79 (m, 2 H) 1.09 (d, J=6.5 Hz, 3 H). MS APCI, m/z=346.1/348.1 HPLC 2.19 min.

According to the analysis of related databases, 114344-60-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTRAZENECA AB; US2008/318943; (2008); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

114344-60-4, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 114344-60-4 name is 2-Amino-3-bromobenzonitrile, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

To a solution of 2-Amino-3-bromobenzonitrile (30.0 g) in THF (240 mL) was added sodium tert-butoxide (1.1 eq.) and the mixture was stirred at -5 to 5C for 1 hour. A solution of intermediate 3a in THF (85.0 g) was then added dropwise and the mixture was stirred for 2-4 hours monitoring the conversion by High Performance Liquid Chromatography (HPLC). Water (210 mL) was then added dropwise and the mixturewas concentrated to remove most of THF. Heptane (300 mL) was then added and the mixture was stirred for 30 mm. After phase separation, the organic layer was washed with water (210 mL), concentrated to 2-3 volumes and filtered through a pad of silica gel (60 g), washing the pad with heptane (300 mL), affording 63.3g of intermediate549.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Amino-3-bromobenzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; STANSFIELD, Ian; QUEROLLE, Olivier Alexis Georges; PONCELET, Virginie Sophie; GROSS, Gerhard Max; JACOBY, Edgar; MEERPOEL, Lieven; KULAGOWSKI, Janusz Jozef; MACLEOD, Calum; MANN, Samuel Edward; GREEN, Simon Richard; HYND, George; (477 pag.)WO2017/125530; (2017); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts